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Flash vacuum pyrolysis of benzylidene halides, benzotrihalides and aryl halides over magnesium
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dc.contributor.author | Aitken, R. Alan | |
dc.contributor.author | Hodgson, Philip K. G. | |
dc.contributor.author | Oyewale, Adebayo O. | |
dc.date.accessioned | 2017-12-31T00:37:09Z | |
dc.date.available | 2017-12-31T00:37:09Z | |
dc.date.issued | 2017-03-30 | |
dc.identifier | 248523975 | |
dc.identifier | f6857859-aabe-4b34-9832-8b1e3fa58dbf | |
dc.identifier | 85009770818 | |
dc.identifier | 000399624500069 | |
dc.identifier.citation | Aitken , R A , Hodgson , P K G & Oyewale , A O 2017 , ' Flash vacuum pyrolysis of benzylidene halides, benzotrihalides and aryl halides over magnesium ' , Journal of analytical and applied pyrolysis , vol. 124 , pp. 618-630 . https://doi.org/10.1016/j.jaap.2016.12.028 | en |
dc.identifier.issn | 0165-2370 | |
dc.identifier.other | ORCID: /0000-0001-6959-5311/work/34857565 | |
dc.identifier.uri | https://hdl.handle.net/10023/12398 | |
dc.description | This work was supported by B.P. | en |
dc.description.abstract | Flash vacuum pyrolysis at 600 °C through glass wool coated with freshly sublimed magnesium is examined as a preparative method for dehalogenative coupling in organic synthesis. Substituted benzylidene chlorides give predominantly the corresponding stilbenes and in some cases these are readily isolated in pure form. With an ortho-halogen substituent, additional cyclisation gives phenanthrenes but the method is not compatible with the presence of several reactive groups. An ortho-methoxy substituent leads to unexpected formation of mono- and dimethyl products. With 1,4-bis(dihalomethyl)benzenes, halogenated polymers are deposited directly from the gas phase via generation of halogenated p-xylylenes. The 1,2- and 1,3-isomers lead respectively to benzocyclobutadiene, isolated as a dimer, and to pyrene. The 1,4-bis(trihalomethyl)benzenes give more highly halogenated polymers directly from the gas phase via halogenated p-xylylenes. While halobenzenes generally give the corresponding benzenes and biphenyls, 1,2-dihalobenzenes additionally produce triphenylene in preparatively useful yield by a process not involving intermediacy of free benzyne. | |
dc.format.extent | 13 | |
dc.format.extent | 578952 | |
dc.language.iso | eng | |
dc.relation.ispartof | Journal of analytical and applied pyrolysis | en |
dc.subject | Flash vacuum pyrolysis | en |
dc.subject | Dehalogenation | en |
dc.subject | Coupling | en |
dc.subject | Polymers | en |
dc.subject | QD Chemistry | en |
dc.subject | NDAS | en |
dc.subject.lcc | QD | en |
dc.title | Flash vacuum pyrolysis of benzylidene halides, benzotrihalides and aryl halides over magnesium | en |
dc.type | Journal article | en |
dc.contributor.institution | University of St Andrews. School of Chemistry | en |
dc.contributor.institution | University of St Andrews. EaSTCHEM | en |
dc.identifier.doi | 10.1016/j.jaap.2016.12.028 | |
dc.description.status | Peer reviewed | en |
dc.date.embargoedUntil | 2017-12-30 |
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